Yeah, progression is a bit of a mess. I had to replay recently cuz my save was broken. But assuming your save isn't old and broken too, events should trigger. Here are some tips:
If you're referring to the bar lady quest, just forget it for a while. For whatever reason you get the quest very early, but can only do it later in the story.
Make sure you have Quests -> Priority set to "none". This can also stop quests from triggering.
In the later stages, there are a couple of girls that you don't get a quest for immediately iirc. One is Haramael's friend Syxia, but you just need to go to her lab after meeting her for the first time. Another is the house AI, you need to keep feeding it etheria.